(17beta)-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estra-1,3,5(10)-triene-3,17-diol
Fulvestrant
CAS: 129453-61-8
Molecular Formula: C32H47F5O3S
(17beta)-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estra-1,3,5(10)-triene-3,17-diol - Names and Identifiers
(17beta)-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estra-1,3,5(10)-triene-3,17-diol - Physico-chemical Properties
| Molecular Formula | C32H47F5O3S |
| Molar Mass | 606.77 |
| Density | 1.201±0.06 g/cm3(Predicted) |
| Melting Point | 104-106°C |
| Boling Point | 674.8±55.0 °C(Predicted) |
| Flash Point | 361.9°C |
| Solubility | DMSO: >5mg/mL |
| Vapor Presure | 3.95E-19mmHg at 25°C |
| Appearance | powder |
| Color | White |
| pKa | 10.27±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
| Refractive Index | 1.521 |
(17beta)-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estra-1,3,5(10)-triene-3,17-diol - Risk and Safety
| WGK Germany | 3 |
| RTECS | KG7623000 |
| HS Code | 2937230000 |
(17beta)-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estra-1,3,5(10)-triene-3,17-diol - Preparation Method
Open Data Verified Data
The corresponding diketene compound was added to Grignard reagent (9-pentafluoropentylthio nonyl bromide was dissolved in tetrahydrofuran solution containing magnesium turnings, and a small amount of iodine was added to initiate the reaction to prepare Grignard reagent). Of the solution. After completion of the reaction, a solution of acetic acid in tetrahydrofuran was added to terminate the reaction. Water was added and tetrahydrofuran was distilled off, followed by further water and extraction with isohexane. After the extract was washed with aqueous potassium chloride, isohexane was distilled off, acetonitrile was added, and copper bromide, lithium bromide and acetic anhydride were slowly added. The reaction solution was placed in a mixture of thiourea, toluene and water, and cooled. The pH was adjusted to 3 with dipotassium hydrogen phosphate. The precipitated copper was removed by filtration. The filter cake was washed with toluene and the organic layers were combined and washed with an aqueous solution of sodium chloride. Toluene was distilled off, methanol was added, and aqueous sodium hydroxide was added and heated. The reaction solution was extracted with isohexane and neutralized with acetic acid. The methanol was distilled off and the resulting material was partitioned between water and ethyl acetate. The organic layer was concentrated, ethyl acetate, acetic acid and hydrogen peroxide were further added, and the reaction was stirred. Ethyl acetate was added and an aqueous solution of sodium sulfite was added to destroy the excess hydrogen peroxide. Neutralization with sodium hydroxide separated the organic layer and washed with water. The solvent was distilled off and seed crystals were added to promote crystallization. The crystals were washed with cold ethyl acetate and recrystallized from ethyl acetate to obtain fulvestrant.
Last Update：2024-01-02 23:10:35
(17beta)-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estra-1,3,5(10)-triene-3,17-diol - Use
Open Data Verified Data
developed by Astrazeneca pharmaceutical company. The US Food and Drug Administration (FDA) approved it for marketing in the US in 2002. Is a new type of ER inhibitor-ER under the prescription of breast cancer treatment drugs. It can bind competitively to ER and its affinity is comparable to that of estradiol. It can also block ER, inhibit its binding to estrogen, and stimulate the receptor to undergo morphological changes, reduce ER concentration, so that tumor cells are damaged. For the treatment of advanced breast cancer that has developed systemic metastasis, for the treatment of postmenopausal metastatic advanced breast cancer that has failed anti-estrogen therapy and is estrogen receptor (ER) positive.
Last Update：2022-01-01 09:09:23
(17beta)-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estra-1,3,5(10)-triene-3,17-diol - Reference Information
| breast cancer treatment drug | fulvestrant is an intramuscular injection drug developed by AstraZeneca. It was approved by the U.S. Food and Drug Administration in April 2002. It is suitable for the treatment of estrogen receptor-positive metastatic breast cancer in postmenopausal women who have deteriorated after anti-estrogen therapy. Many breast cancer cells have estrogen receptors (ER), which stimulate the growth of such tumors. Fluvestrant is a "pure" estrogen receptor antagonist with no partial estrogen-like agonistic effects. It inhibits the estrogen signaling pathway by binding, blocking and down-regulating the ER, and can compete with the ER The affinity with ER is close to estrogen, which is 100 times that of tamoxifen. It is the only anti-estrogen drug that can be widely used in clinical practice after the failure of tamoxifen, because the drug is endocrine therapy, it will not cause common adverse reactions of chemotherapy, so it has good patient compliance. Many clinical studies have found that the 250mg dose of fulvestrant has good therapeutic effect and stable safety in the second-line treatment of advanced breast cancer. |
| Mechanism of action | Fluvestrant is a steroid anti-estrogen drug. Its chemical structure is similar to estradiol. The difference is that it is at the 7α position. There is a linking group; it is an alkylamine analog of 17 β-estradiol, which can antagonize estrogen by occupying the ER and inhibit the activation of genes stimulated by this estrogen, therefore, estrogen-related processes necessary to affect cell circulation; its affinity with ER is close to estrogen, but it is 100 times that of tamoxifen. Apoptosis is crucial in maintaining homeostasis, and it may also be another major mechanism of the therapeutic effect of fulvestrant. |
| estrogen receptor antagonist | The breast cancer treatment drug fluvestrant developed by AstraZeneca Company is an estrogen receptor antagonist with low side effects. Its appearance means a major breakthrough in breast cancer treatment. Studies have shown that bone cells have typical estrogen receptors (ERs), and low estrogen status can lead to bone resorption and osteoporosis. Although fulvestrant has pure antagonistic activity, studies on ovariectomized rats show that it has no estrogen-like or anti-estrogen effect, while tamoxifen has estrogen-like effect and reduces periosteal formation. The fulvestrant also has significant activity against certain target organs other than breast tissue. For the endometrium, tamoxifen has partial agonistic activity, which will increase the incidence of endometrial cancer. However, the animal experiment of fulvestrum group did not show this adverse reaction. It not only shows a lack of activity on the uterus, but also It can block the mitogenic effect of tamoxifen on ovariectomized and estrogen-treated monkeys. |
| pharmacological effects | fulvestrant has relatively poor oral bioavailability, so it usually uses lipids as excipients for intramuscular injection. An open, randomized, multi-center study conducted in postmenopausal women with advanced breast cancer showed that there was no significant difference in pharmacokinetics and toxic side effects by injecting 250 mg of this product with a 5 ml or two 2.5 ml. The blood drug concentration was dose-dependent and individual differences; during the treatment period of 7 days, there was no significant change in serum LH, FSH or SBHG levels; the drug did not pass through the blood-brain barrier, it will not cause side effects such as vasomotor. Theoretically, estrogen inactivation can lead to an increase in bone turnover and promote osteoporosis. However, this effect has not been found in animal models, and fulvestrant has not caused an increase in bone turnover replacement markers. |
| adverse reactions | fulvestrant has fewer side effects, such as transient vaginal bleeding, body odor changes and sleepwalking state. However, there are no reports such as vaginal dryness, weight gain, abnormal blood coagulation, thrombosis and changes in libido, and facial flushing and sweating have not changed. A small phase III clinical trial showed that 19 women with metastatic breast cancer used this product. The clinical effective rate was 67%, and there were no serious safety problems, but it must be continuously injected monthly, and it is well tolerated. Only slight redness and pain occurred at the injection site. The subjects' facial flushing, endometrial thickness, sex hormone binding globulin levels, follicle stimulating hormone levels and luteinizing hormone levels did not change. |
| Production method | Add the corresponding dienone compound to the Grignard reagent (9-pentafluoropentyl thionyl bromide dissolved in the tetrahydrofuran solution containing magnesium chips, Add a small amount of iodine to initiate the reaction to prepare the Grignard reagent) solution. After the reaction is complete, the tetrahydrofuran solution with acetic acid is added to stop the reaction. Add water, evaporate tetrahydrofuran, add water, and extract with isohexane. After the extract is washed with potassium chloride aqueous solution, isohexane is distilled, acetonitrile is added, and copper bromide, lithium bromide and acetic anhydride are slowly added. The reaction liquid is put into a mixture of thiourea, toluene and water and cooled. Adjust the pH to 3 with dipotassium hydrogen phosphate, and filter to remove the precipitated copper. The filter cake is washed with toluene, the organic layers are combined, and washed with sodium chloride aqueous solution. Evaporate toluene, add methanol, add sodium hydroxide aqueous solution, and heat. The reaction solution is extracted with isohexane and neutralized with acetic acid. The methanol is distilled, and the resulting substance is distributed between water and ethyl acetate. Concentrate the organic layer, add ethyl acetate, acetic acid and hydrogen peroxide, and stir for reaction. Add ethyl acetate, and then add sodium sulfite aqueous solution to destroy excess hydrogen peroxide. Neutralize with sodium hydroxide, separate the organic layer, and wash with water. The solvent is distilled and seed crystals are added to promote crystallization. The crystallization is washed with cold ethyl acetate, and then recrystallized with ethyl acetate to obtain fulvestrant. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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Product Name: Fulvestrant Request for quotation
CAS: 129453-61-8
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